Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide

• Yuzo Nakamura,
• Motohiro Fujiu,
• Tatsuya Murase,
• Yoshimitsu Itoh,
• Hiroki Serizawa,
• Kohsuke Aikawa and
• Koichi Mikami

Beilstein J. Org. Chem. 2013, 9, 2404–2409, doi:10.3762/bjoc.9.277

• , biological, and physical properties [1][2][3][4][5][6]. Particularly, trifluoromethylated compounds can be widely employed as one of the most effective analogues of bioactive compounds, because the trifluoromethyl group enhances the metabolic stability, lipophilicity, and bioavailability of these compounds

One-pot sequential synthesis of isocyanates and urea derivatives via a microwave-assisted Staudinger–aza-Wittig reaction

• Diego Carnaroglio,
• Katia Martina,
• Giovanni Palmisano,
• Andrea Penoni,
• Claudia Domini and
• Giancarlo Cravotto

Beilstein J. Org. Chem. 2013, 9, 2378–2386, doi:10.3762/bjoc.9.274

• [1]. Isocyanates play a relevant role as chemical intermediates in the manufacturing of thermoplastic foams, elastomers, adhesives, agrochemicals and pharmaceuticals. The isocyanate group is also widely used as a precursor to several bioactive compounds and drugs that contain urea and carbamate

The chemistry of isoindole natural products

• Klaus Speck and
• Thomas Magauer

Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243

• alkaloids are highly bioactive compounds [167][168]. The diverse spectrum includes vasodilatoring, anti-arrhythmic, immunomodulating and analgesic activities. Hetisines can be classified, according to Wang and Liang, as C20-diterpenoid alkaloids, which belong to the family of atisane alkaloids [167]. The

Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans

• Yifan Li and
• Jérôme Waser

Beilstein J. Org. Chem. 2013, 9, 1763–1767, doi:10.3762/bjoc.9.204

• successful in the case of the more complex drug 8-methoxypsoralen (8-MOP). Keywords: alkynylation; benzofurans; cooperative catalysis; direct functionalization; gold catalysis; hypervalent iodine; Introduction Benzofurans are important heterocycles frequently encountered in both bioactive compounds and

• [1][2][3][4]. The natural product coumestrol (4) is found especially in soy beans and has estrogenic activity [5]. Synthetic bioactive compounds containing benzofurans are also important, as exemplified by amiodarone (5), as antiarrythmic drug [6][7]. Finally, benzofurans have also emerged recently

• silica gel and purified directly by column chromatography. Benzofurans in bioactive compounds and materials. Zinc–gold catalyzed C2-alkynylation of benzofurans. Scope of the reaction. Alkynylation of 7-methoxybenzofuran (7j) [31]. Alkynylation of 8-methoxypsoralen (2). Optimization of the alkynylation of

Palladium(II)-catalyzed Heck reaction of aryl halides and arylboronic acids with olefins under mild conditions

• Tanveer Mahamadali Shaikh and
• Fung-E Hong

Beilstein J. Org. Chem. 2013, 9, 1578–1588, doi:10.3762/bjoc.9.180

• Substituted olefins are important structural motifs in natural products, pharmaceuticals, bioactive compounds and organic materials [1][2]. Olefins such as stilbene derivatives normally show antitumor [3], antiinflammatory [4], neuroprotective [5], and cardioprotective [6] properties. Due to its importance in

Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production

• Sándor B. Ötvös,
• Ádám Georgiádes,
• István M. Mándity,
• Lóránd Kiss and
• Ferenc Fülöp

Beilstein J. Org. Chem. 2013, 9, 1508–1516, doi:10.3762/bjoc.9.172

• skeleton is frequently used as a pharmacophore for the modification of known pharmaceuticals. Triazole analogues of several bioactive compounds have recently been reported. Examples are those of the well-known highly functionalized antiviral cyclic amino acid derivatives oseltamivir and zanamivir (5 and 6

Practical synthesis of indoles and benzofurans in water using a heterogeneous bimetallic catalyst

• Cybille Rossy,
• Eric Fouquet and
• François-Xavier Felpin

Beilstein J. Org. Chem. 2013, 9, 1426–1431, doi:10.3762/bjoc.9.160

• procedure allows the preparation of heterocycles with good yields and is tolerant to a wide variety of functional groups. Keywords: benzofuran; bimetallic catalyst; heterogeneous catalysis; indole; water; Introduction Heterocycles are ubiquitous building blocks in natural products, bioactive compounds and

Catalytic asymmetric tandem Friedel–Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans

• Jiahuan Peng and
• Da-Ming Du

Beilstein J. Org. Chem. 2013, 9, 1210–1216, doi:10.3762/bjoc.9.137

• -linked bis(oxazoline)-Zn(II) complexes. On the other hand, indole and its derivatives are one of the most intensively investigated classical heterocycles owing to their prevalence in bioactive compounds. Indoles have been successfully utilized in asymmetric Friedel–Crafts reactions with nitroolefin and

Short synthesis of the common trisaccharide core of kankanose and kankanoside isolated from Cistanche tubulosa

• Goutam Guchhait and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2013, 9, 705–709, doi:10.3762/bjoc.9.80

• . tubulosa), an Orobanchaceae parasitic plant found in Africa, Asia and Arabia, has been traditionally used as folk medicine and tonic for the treatment of blood-circulation-related disorders, impotence, sterility and body weakness [1][2][3]. A significant number of bioactive compounds have been isolated

A one-pot catalyst-free synthesis of functionalized pyrrolo[1,2-a]quinoxaline derivatives from benzene-1,2-diamine, acetylenedicarboxylates and ethyl bromopyruvate

• Mohammad Piltan,
• Loghman Moradi,
• Golaleh Abasi and
• Seyed Amir Zarei

Beilstein J. Org. Chem. 2013, 9, 510–515, doi:10.3762/bjoc.9.55

• of various bioactive compounds that possess antibiotic, anti-inflammatory, antimicrobial [5], antidiabetic [6], and antiviral activity against retroviruses including HIV [7]. In addition, quinoxaline derivatives are also associated with a wide spectrum of biological effects including anticancer [8

N-Heterocyclic carbene–palladium catalysts for the direct arylation of pyrrole derivatives with aryl chlorides

• Ismail Özdemir,
• Nevin Gürbüz,
• Nazan Kaloğlu,
• Öznur Doğan,
• Murat Kaloğlu,
• Christian Bruneau and
• Henri Doucet

Beilstein J. Org. Chem. 2013, 9, 303–312, doi:10.3762/bjoc.9.35

• conversion of the aryl chloride. The solvent was removed by heating of the reaction vessel under vacuum and the residue was charged directly onto a silica-gel column. The products were eluted by using an appropriate ratio of diethyl ether and pentane. Examples of pyrrole-containing bioactive compounds

Inclusion of the insecticide fenitrothion in dimethylated-β-cyclodextrin: unusual guest disorder in the solid state and efficient retardation of the hydrolysis rate of the complexed guest in alkaline solution

• Dyanne L. Cruickshank,
• Natalia M. Rougier,
• Raquel V. Vico,
• Susan A. Bourne,
• Elba I. Buján,
• Mino R. Caira and
• Rita H. de Rossi

Beilstein J. Org. Chem. 2013, 9, 106–117, doi:10.3762/bjoc.9.14

• in this and previous studies that we have undertaken, give indications of which type of cyclodextrin may be best suited in an agrochemical formulation to ensure resistance of sensitive bioactive compounds to chemical degradation, thus maximising their intended biological effect. Thermodynamic data

Hydrophobic analogues of rhodamine B and rhodamine 101: potent fluorescent probes of mitochondria in living C. elegans

• Laurie F. Mottram,
• Safiyyah Forbes,
• Brian D. Ackley and
• Blake R. Peterson

Beilstein J. Org. Chem. 2012, 8, 2156–2165, doi:10.3762/bjoc.8.243

• permeability of this animal to small molecules. For example, many bioactive compounds require at least a 10-fold higher dose to exhibit activity in C. elegans compared to other organisms [30], due to a number of physical and enzymatic barriers to entry of small molecules. On the exterior surface of C. elegans

Bioactive selaginellins from Selaginella tamariscina (Beauv.) Spring

• Chao Yang,
• Yutian Shao,
• Kang Li and
• Wujiong Xia

Beilstein J. Org. Chem. 2012, 8, 1884–1889, doi:10.3762/bjoc.8.217

• circulation [3]. Phytochemical and pharmacological studies on genus Selaginella led to identifications of numerous bioactive compounds, including biflavonoids, alkaloids, and lignans, with broad biological activities, including antivirus, antifungal, antibacterial, cytotoxic, and anti-inflammatory properties

Copper-catalyzed CuAAC/intramolecular C–H arylation sequence: Synthesis of annulated 1,2,3-triazoles

• Rajkumar Jeyachandran,
• Harish Kumar Potukuchi and
• Lutz Ackermann

Beilstein J. Org. Chem. 2012, 8, 1771–1777, doi:10.3762/bjoc.8.202

• ; heteroarenes; triazoles; Introduction Transition-metal-catalyzed C–H bond functionalizations are increasingly viable tools for step-economical syntheses of various valuable bioactive compounds [1][2][3], which avoid the preparation and use of preactivated substrates [4][5][6][7][8][9][10][11][12][13][14][15

Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach

• Florian Boeck,
• Max Blazejak,
• Markus R. Anneser and
• Lukas Hintermann

Beilstein J. Org. Chem. 2012, 8, 1630–1636, doi:10.3762/bjoc.8.186

• -hydroxycinnamates, followed by the phosphane catalyzed cyclization. Keywords: catalysis; coumarins; heterocycles; mechanisms; organocatalysis; phosphanes; Introduction Coumarins are important structural motifs in natural products and bioactive compounds, in which they exhibit broad biological activity, e.g., as

Synthesis and in silico screening of a library of β-carboline-containing compounds

• Kay M. Brummond,
• John R. Goodell,
• Matthew G. LaPorte,
• Lirong Wang and
• Xiang-Qun Xie

Beilstein J. Org. Chem. 2012, 8, 1048–1058, doi:10.3762/bjoc.8.117

• protein binding pockets to identify favorable compound–protein interactions. A second approach is a ligand-based strategy in which the structural similarities between a query compound and a collection of bioactive compounds are identified. In the present study, both of these strategies were used to

• [16][17]. In this study, structural similarities were calculated between the compounds of the β-carboline library and the bioactive compounds in the well-annotated database, ChEMBL version 13, the largest publicly available compound-target database, containing 1,143,682 distinct compounds, 8,845

Unprecedented deoxygenation at C-7 of the ansamitocin core during mutasynthetic biotransformations

• Tobias Knobloch,
• Gerald Dräger,
• Wera Collisi,
• Florenz Sasse and
• Andreas Kirschning

Beilstein J. Org. Chem. 2012, 8, 861–869, doi:10.3762/bjoc.8.96

• transformed into bioactive compounds 3–5 by a set of post-PKS tailoring steps, following a predetermined, only partly flexible logic (Scheme 1) [16]. Complementing our studies with mutant strain A. pretiosum HGF073, blocked in the biosynthesis of the PKS starter unit AHBA 1 [13][14][15][16], we recently

Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester

• Sarah L. Harding,
• Sebastian M. Marcuccio and
• G. Paul Savage

Beilstein J. Org. Chem. 2012, 8, 606–612, doi:10.3762/bjoc.8.67

• alkenes [15], alkynes [16][17], and benzyne [18][19], to give Δ2-isoxazolines and isoxazoles. These are interesting sources of bioactive compounds in their own right, but isoxazoles are particularly valuable for their latent functionality as β-hydroxyketones, β-aminoalcohols, 1,3-diols, and a range of

Volatile organic compounds produced by the phytopathogenic bacterium Xanthomonas campestris pv. vesicatoria 85-10

• Teresa Weise,
• Marco Kai,
• Anja Gummesson,
• Armin Troeger,
• Stephan von Reuß,
• Silvia Piepenborn,
• Francine Kosterka,
• Martin Sklorz,
• Ralf Zimmermann,
• Wittko Francke and
• Birgit Piechulla

Beilstein J. Org. Chem. 2012, 8, 579–596, doi:10.3762/bjoc.8.65

• ] and, therefore, cannot be considered as a growth-promoting or -inhibitory component. Considerations concerning methodological approaches It is quite obvious that further research is necessary to identify the bioactive compounds, especially those sensitive and/or highly volatile substances that escaped

Carbamate derivatives and sesquiterpenoids from the South China Sea gorgonian Melitodes squamata

• Li-Si Huang,
• Fei He,
• Hui Huang,
• Xiao-Yong Zhang and
• Shu-Hua Qi

Beilstein J. Org. Chem. 2012, 8, 170–176, doi:10.3762/bjoc.8.18

• nerves, and calming scare, etc [3]. A previous study on the chemical constituents of Melithaea family gorgonians led to the isolation of four new steroids melithasterols A–D from Melithaea ocracea [4]. Results and Discussion In order to further obtain new bioactive compounds from gorgonians, we studied

Synthesis of highly functionalized β-aminocyclopentanecarboxylate stereoisomers by reductive ring opening reaction of isoxazolines

• Melinda Nonn,
• Loránd Kiss,
• Reijo Sillanpää and
• Ferenc Fülöp

Beilstein J. Org. Chem. 2012, 8, 100–106, doi:10.3762/bjoc.8.10

• isoxazoline-fused cyclic β-amino esters to multifunctionalized 2-aminocyclopentanecarboxylates through the use of NaBH4/NiCl2 as reducing agent. As Peramivir related derivatives, highly functionalized cyclic amino esters may be regarded as promising bioactive compounds. Experimental The chemicals were

Synthetic approaches to multifunctional indenes

• Neus Mesquida,
• Sara López-Pérez,
• Immaculada Dinarès and
• Ermitas Alcalde

Beilstein J. Org. Chem. 2011, 7, 1739–1744, doi:10.3762/bjoc.7.204

• ][9]. In addition, indene-based structures are a source of bioactive compounds in drug discovery and development [10][11][12][13][14][15][16][17][18]. The routes to access multiply substituted indenes with at least two different functional groups (FGs) are generally complex, and the synthetic

• elaboration of a variety of indene-based molecular modules with applications in fields as diverse as bioactive compounds, ligand precursors for metallocene catalyst systems, and functional materials. Key NMR responses for compounds 17, 19 and 23: 1D NOESY experiments. Retrosynthetic pathways to 3,5

Tertiary alcohol preferred: Hydroxylation of trans-3-methyl-L-proline with proline hydroxylases

• Christian Klein and
• Wolfgang Hüttel

Beilstein J. Org. Chem. 2011, 7, 1643–1647, doi:10.3762/bjoc.7.193

• approach whose potential has not yet been fully exploited is the stereospecific hydroxylation of tertiary alkyl moieties with oxygenases. Most oxidations to tertiary alcohols described so far were observed during degradation of steroids and other terpenoid bioactive compounds by microbial whole cells [10

Natural product biosyntheses in cyanobacteria: A treasure trove of unique enzymes

• Jan-Christoph Kehr,
• Douglas Gatte Picchi and
• Elke Dittmann

Beilstein J. Org. Chem. 2011, 7, 1622–1635, doi:10.3762/bjoc.7.191

• obtained from the biochemical studies of cyanobacterial pathways can inspire the development of concepts for the design of bioactive compounds by synthetic-biology approaches in the future. Keywords: cyanobacteria; natural products; NRPS; PKS; ribosomal peptides; Introduction The role of cyanobacteria in